Jenner opened up about the first time she tried to transition in a video shown at Makers Conference in Rancho Palos Verdes on Tuesday, where Caitlyn did a Q&A.

After two divorces in a scant five years (from Chrystie Scott in 1981 and from Linda Thompson in 1986), Jenner said she had some soul searching to do.

"I got a house in Malibu. I basically stayed there for six years. I really started struggling with my identity, about 'who am I?'" Caitlyn said. "I started doing things to make me feel better about myself, started doing hormones. But yeah, I was a good 36B. I loved them, you know, I thought: 'This is fabulous.'”

Her original goal was to transition by 40 but, when she was 39, she found that she couldn’t go through with it. She met the future Kris Jenner and the pair hit it off. Caitlyn, who then went by Bruce, was honest from the start.

“I had to be,” Caitlyn said, “I was a 36B."

After she and Kris had children, Kylie and Kendall, whom Caitlyn says are her “greatest accomplishment,” Caitlyn decided her family took priority over her transition.

"Everything [with the transition was] really heading the right direction, and I made this decision to kind of move on [with] my life and Kris and I together and this family," Caitlyn said. "'Okay, I've got to get rid of these gender things and get off hormones and this and that.' I actually had my boobs removed. I never told anybody that."

Kris and Caitlyn set some boundaries for Caitlyn’s gender expression.

"The rules, kind of, with Kris and I [were]: 'Don't dress up, certainly [not] around the house. If you really need to do that, when you're on the road take stuff and do that,'" Caitlyn said. "So I did that for years."

The video also covers Caitlyn’s rise to Olympic fame and her thoughts of suicide as she first faced public scrutiny around her transition.